Field of the Invention
This invention is directed to new organic compounds and is particularly concerned with novel 1-substituted 6-phenyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepines and a process for the production thereof.
The novel compounds and the process of production therefor can be illustratively represented as follows: ##STR4## wherein R.sub.o is hydrogen, methyl, ethyl, chlorine, fluorine, or bromine; wherein X is fluorine, bromine or chlorine; wherein X" is bromine or chlorine; wherein R', R", and R''' are alkyl of 1 to 3 carbon atoms, inclusive, wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl defined as above, wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are selected from the group consisting of hydrogen, alkyl as defined above, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, and alkylsulfonyl, in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, and wherein R.sub.6 is hydrogen, methyl, or ethyl.
The process of this invention comprises: treating a selected 5-phenyl-3H-1,4-benzodiazepin-2-yl hydrazine (1) with a halo or dihalo acylhalide in a solvent in the presence of a base to give the corresponding 1-substituted-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepi ne. The 1-substituted compounds in which the substitutent is ##STR5## wherein X is chlorine or bromine and R.sub.6 is defined as above, can be treated with sodium cyanide to give the cyanide analogue (III); or it can be treated with a dialkylamine to give the 1-(dialkylamino)alkyl compound IV, or treated with a alkylmercaptan to give a 1-alkyl-thioalkyl compound (V).